methyl (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate | 197297-83-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate
• 英文别名: methyl (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methylpent-2-enoate
• CAS: 197297-83-9
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: IJZYONJBQJUHND-ZHACJKMWSA-N

物化性质

• 沸点：
  420.6±45.0 °C(predicted)
• 密度：
  1.026±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methylpent-2-en-1-ol
  参考文献：
  名称：

  Preparation of Enantiopure Precursors for the Vitamin E Synthesis. A Comparison of the Asymmetric Allylation of Ketones and the Sharpless Bishydroxylation

  摘要：

  本文介绍了前体 9、10、16 和 17 的对映体选择性合成，通过酮 6 的不对称烯丙基化和脂族烯 11 和 15 的 Sharpless 双羟基化，可以制备对映体纯维生素 E。

  DOI：

  10.1055/s-1997-1522
• 作为产物：
  描述：

  1,4-dimethoxy-2,3,5-trimethyl-benzene 在 platinum(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 硫酸 、 氢气 、 碘 、 戴斯-马丁氧化剂 、 高碘酸 、 二乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 45.0~55.0 ℃ 、303.98 kPa 条件下， 反应 22.0h， 生成 methyl (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate
  参考文献：
  名称：

  Enantioselective Synthesis of the Chromane Moiety of Vitamin E

  摘要：

  Several new approaches for the enantioselective synthesis of the chromane moiety of vitamin E are described. Sonogashira coupling of 3a with the alkyne 4 and subsequent elimination gave 6, which was bis(hydroxylated) in 93% yield and with 85% ee. Recrystallization gave enantiopure 7a, which was hydrogenated and transformed into the vitamin E precursor 11. The bis(hydroxylation) of 18 and 21 to give 9 and 22, respectively, was less than satisfactory, proceeding with ee values of 28% and 18%. In contrast, stereoselective allylation of ketone 15 followed by removal of the protecting group or ozonolysis of the allyl moiety furnished the allyl alcohol 26 and the aldehyde 27, respectively, in almost enantiopure form, which again could be used as precursors for vitamin E. Partial hydrogenation of 5a gave the alkene 32a and that of 28 the alkene 30b, both of which show interesting atropisomerism.

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1075::aid-ejoc1075>3.0.co;2-i

文献信息

• Preparation of Enantiopure Precursors for the Vitamin E Synthesis. A Comparison of the Asymmetric Allylation of Ketones and the Sharpless Bishydroxylation
  作者：Lutz Tietze、Jochen Görlitzer

  DOI：10.1055/s-1997-1522

  日期：1997.9

  The enantioselective synthesis of the precursors 9, 10, 16 and 17 allow for the preparation of enantiopure vitamin E by asymmetric allylation of the ketone 6 and Sharpless bishydroxylation of the aliphatic alkenes 11 and 15 is described.

  本文介绍了前体 9、10、16 和 17 的对映体选择性合成，通过酮 6 的不对称烯丙基化和脂族烯 11 和 15 的 Sharpless 双羟基化，可以制备对映体纯维生素 E。
• Enantioselective Synthesis of the Chromane Moiety of Vitamin E
  作者：Lutz F. Tietze、Jochen Görlitzer、Ansgar Schuffenhauer、Matthias Hübner

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1075::aid-ejoc1075>3.0.co;2-i

  日期：1999.5

  Several new approaches for the enantioselective synthesis of the chromane moiety of vitamin E are described. Sonogashira coupling of 3a with the alkyne 4 and subsequent elimination gave 6, which was bis(hydroxylated) in 93% yield and with 85% ee. Recrystallization gave enantiopure 7a, which was hydrogenated and transformed into the vitamin E precursor 11. The bis(hydroxylation) of 18 and 21 to give 9 and 22, respectively, was less than satisfactory, proceeding with ee values of 28% and 18%. In contrast, stereoselective allylation of ketone 15 followed by removal of the protecting group or ozonolysis of the allyl moiety furnished the allyl alcohol 26 and the aldehyde 27, respectively, in almost enantiopure form, which again could be used as precursors for vitamin E. Partial hydrogenation of 5a gave the alkene 32a and that of 28 the alkene 30b, both of which show interesting atropisomerism.